Chicago Historical & Heritage Tours

Chicago Historical & Heritage Tours

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Chicago Crime and Mob Tour

4.5 star rating: Recommended 168 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $35.95
$39.95 Save $4.00

Chicago Prohibition Tour

5 star rating: Highly Recommended 39 Reviews

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $44.99

Chicago Walking Tour: Inside the Architecture of the Loop

5 star rating: Highly Recommended 28 Reviews

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Chicago Walking Tour: Historic Skyscrapers

5 star rating: Highly Recommended 20 Reviews

Perhaps Chicago's most identifiable claim to fame resides in its architecture. The prototype of the modern industrial metropolis arose from the ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00
$23.00 Save $5.00

Chicago Walking Tour: Art Deco Skyscrapers

4.5 star rating: Recommended 29 Reviews

Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour. Learn ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00
$23.00 Save $5.00

Chicago Barrel Bus Prohibition Themed Gangster Tour

Take a 2-hour barrel bus adventure through the historic streets of Chicago on our Gangster Tour. Experience the rich chronicles of Chicagoland’s most ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $35.00

Chicago Gangster Tour

Chicago has a long history of organized crime and was famously home to the American mafia figure Al Capone. In 1850, Chicago had a population of 80,000 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $35.00

Chicago Walking Tour: Modern Architecture

5 star rating: Highly Recommended 7 Reviews

Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00
$23.00 Save $5.00

Pullman National Monument Bus Tour

Step back in time and explore with us one this exclusive bus tour one of America's truly unique enclaves.  The Pullman District is located on Chicago's ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $30.00

Telling the Story Walking Tour

Explore Chicago by walking through the foundations of modern architecture itself, from the "Father of the Skyscraper" to Chicago's very own style.

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Creating the Melting Pot Walking Tour

Though all of Chicago’s neighborhoods are, of course, culturally rich, the West Loop is perhaps the closest and most accessible to visitors who would ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

World's Fair Bus Tour

Relive the grandeur and magic of Chicago's two world's fairs on this one-of-a-kind bus tour that is the only tour in the city that recreates both fairs for ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $30.00

Rebuilding the Second City Walking Tour

River North, one of the oldest neighborhoods in Chicago, has experienced unparalleled evolution over the past 200 years – and Inside Chicago Walking ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Haunted Chicago Segway Tour

5 star rating: Highly Recommended 13 Reviews

Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a Segway at night! Venture through the dark with your ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $70.85

The Roaring 20's Art Deco and Decadence Tour

The late 1920s-early 1930s was a heady time in Chicago. The hot jazz and secret speakeasies that kept nightlife ablaze – despite Prohibition – ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $59.00

1960's Nightlife in the Gold Coast Tour

On this tour we are all about going back in time to experience the Chicago of an earlier era. And one of the most exciting eras to explore is the mid-twentieth ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $59.00

1950's Nightlife in the Loop Tour

Intelligent architecture tours of Chicago for intelligent adults, we combine serious history with entertaining immersion in the past.  Experience ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $59.00

Macy's State Street Historical Store Tour

Experience a historic store tour of Macy’s on State Street and learn how Macy’s has become America’s largest department store, with over 800 locations and ...  Read more

Location: Chicago, Illinois
Duration: 60 minutes

From USD $12.00

The In The Loop Tour of Chicago

The “In The Loop” Tour is everything you want to know about Chicago all rolled into one fabulous walking tour. It’s architecture! History! ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00
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